CA2391785C - Improved solvent systems - Google Patents
Improved solvent systems Download PDFInfo
- Publication number
- CA2391785C CA2391785C CA002391785A CA2391785A CA2391785C CA 2391785 C CA2391785 C CA 2391785C CA 002391785 A CA002391785 A CA 002391785A CA 2391785 A CA2391785 A CA 2391785A CA 2391785 C CA2391785 C CA 2391785C
- Authority
- CA
- Canada
- Prior art keywords
- carrier
- solvent system
- hydrochloride
- amine
- phosphorus
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000002904 solvent Substances 0.000 title claims abstract description 23
- -1 phosphorus halide Chemical class 0.000 claims abstract description 20
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 15
- 239000011574 phosphorus Substances 0.000 claims abstract description 15
- 229940122361 Bisphosphonate Drugs 0.000 claims abstract description 13
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000004663 bisphosphonates Chemical class 0.000 claims abstract description 10
- 150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 10
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 6
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 238000011065 in-situ storage Methods 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 150000002148 esters Chemical group 0.000 claims description 3
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 claims description 2
- 239000005703 Trimethylamine hydrochloride Substances 0.000 claims description 2
- 150000004820 halides Chemical group 0.000 claims description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical group ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- KLBOFRLEHJAXIU-UHFFFAOYSA-N tributylazanium;chloride Chemical compound Cl.CCCCN(CCCC)CCCC KLBOFRLEHJAXIU-UHFFFAOYSA-N 0.000 claims description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 claims description 2
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 claims description 2
- BMXILUZRCXPKOI-UHFFFAOYSA-N tripropylazanium;chloride Chemical group Cl.CCCN(CCC)CCC BMXILUZRCXPKOI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000477 aza group Chemical group 0.000 claims 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- 239000007787 solid Substances 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- 239000000969 carrier Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- PUUSSSIBPPTKTP-UHFFFAOYSA-N neridronic acid Chemical compound NCCCCCC(O)(P(O)(O)=O)P(O)(O)=O PUUSSSIBPPTKTP-UHFFFAOYSA-N 0.000 description 1
- 229950010733 neridronic acid Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- CAKRAHQRJGUPIG-UHFFFAOYSA-M sodium;[4-azaniumyl-1-hydroxy-1-[hydroxy(oxido)phosphoryl]butyl]-hydroxyphosphinate Chemical compound [Na+].NCCCC(O)(P(O)(O)=O)P(O)([O-])=O CAKRAHQRJGUPIG-UHFFFAOYSA-M 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/5532—Seven-(or more) membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3839—Polyphosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3839—Polyphosphonic acids
- C07F9/3873—Polyphosphonic acids containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Cyclones (AREA)
- Photographic Developing Apparatuses (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0115824.5 | 2001-06-28 | ||
| GBGB0115824.5A GB0115824D0 (en) | 2001-06-28 | 2001-06-28 | Improved solvent systems |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2391785A1 CA2391785A1 (en) | 2002-12-28 |
| CA2391785C true CA2391785C (en) | 2008-11-18 |
Family
ID=9917538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002391785A Expired - Lifetime CA2391785C (en) | 2001-06-28 | 2002-06-27 | Improved solvent systems |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6878846B2 (de) |
| EP (1) | EP1364956B8 (de) |
| AT (1) | ATE334994T1 (de) |
| CA (1) | CA2391785C (de) |
| DE (1) | DE60213566T2 (de) |
| GB (2) | GB0115824D0 (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20020908A1 (it) | 2002-04-29 | 2003-10-29 | Chemi Spa | Processo di preparazione di sodio alendronato |
| CA2485443C (en) * | 2002-05-17 | 2010-04-06 | Teva Pharmaceutical Industries Ltd | Use of aromatic hydrocarbons and silicone fluids for making bisphosphonic acids |
| PT1656386E (pt) | 2003-08-21 | 2010-03-05 | Sun Pharmaceuticals Ind Ltd | Processo para a preparação de compostos de ácido bifosfónico |
| US8003820B2 (en) * | 2005-10-20 | 2011-08-23 | Dr. Reddy's Laboratories Limited | Process for preparing bisphosphonic acids |
| WO2007132478A2 (en) * | 2006-05-11 | 2007-11-22 | Ind-Swift Laboratories Limited | Process for the preparation of pure risedronic acid or salts |
| CA2689504A1 (en) * | 2007-06-19 | 2008-12-24 | Albemarle Corporation | Processes for manufacturing bisphosphonic acids |
| EA201270328A1 (ru) * | 2009-08-28 | 2012-09-28 | Синтон Б. В. | Способ получения 1-гидроксиалкилиден-1,1-дифосфоновых кислот |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4835948B1 (de) | 1968-11-04 | 1973-10-31 | ||
| JPS5234746B2 (de) * | 1972-12-27 | 1977-09-05 | ||
| DE3016289A1 (de) * | 1980-04-28 | 1981-10-29 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung von omega -amino-1-hydroxyalkyliden-1,1-bis-phosphonsaeuren |
| DD152352A1 (de) * | 1980-08-01 | 1981-11-25 | Karlheinz Koch | Verfahren zur herstellung strahlenchemisch haertbarer reaktionsharzmassen |
| DE3700772A1 (de) * | 1987-01-13 | 1988-07-21 | Inst Khim Kinetiki I Gorenija | Verfahren zur herstellung von i-funktionellsubstituierten alkyliden-i,i-diphosphonsaeuren und deren gemischen |
| US5019651A (en) * | 1990-06-20 | 1991-05-28 | Merck & Co., Inc. | Process for preparing 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid (ABP) or salts thereof |
| GB9325113D0 (en) * | 1993-12-08 | 1994-02-09 | Albright & Wilson | Substituted phosphonic acids |
| FR2749775B1 (fr) * | 1996-06-13 | 1998-07-24 | Ceca Sa | Procede de traitement d'engrais par compositions hydrophobantes/antimottantes en vue de leur stockage en vrac |
| CA2197267C (en) * | 1997-02-11 | 2000-02-08 | Yong Tao | Process for the production of 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid or salts thereof |
| RU2179152C2 (ru) * | 2000-01-31 | 2002-02-10 | Институт органической и физической химии им. А.Е. Арбузова Казанского научного центра РАН | Способ получения фосфористой кислоты (варианты) |
| US6562974B2 (en) * | 2000-02-01 | 2003-05-13 | The Procter & Gamble Company | Process for making geminal bisphosphonates |
-
2001
- 2001-06-28 GB GBGB0115824.5A patent/GB0115824D0/en not_active Ceased
-
2002
- 2002-05-21 AT AT02253548T patent/ATE334994T1/de not_active IP Right Cessation
- 2002-05-21 DE DE60213566T patent/DE60213566T2/de not_active Expired - Lifetime
- 2002-05-21 GB GB0211589A patent/GB2378444B/en not_active Expired - Fee Related
- 2002-05-21 EP EP02253548A patent/EP1364956B8/de not_active Expired - Lifetime
- 2002-06-21 US US10/177,130 patent/US6878846B2/en not_active Expired - Lifetime
- 2002-06-27 CA CA002391785A patent/CA2391785C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US20030013918A1 (en) | 2003-01-16 |
| EP1364956B1 (de) | 2006-08-02 |
| DE60213566T2 (de) | 2007-10-04 |
| US6878846B2 (en) | 2005-04-12 |
| CA2391785A1 (en) | 2002-12-28 |
| GB2378444B (en) | 2005-06-15 |
| GB2378444A (en) | 2003-02-12 |
| GB0115824D0 (en) | 2001-08-22 |
| EP1364956A1 (de) | 2003-11-26 |
| DE60213566D1 (de) | 2006-09-14 |
| GB0211589D0 (en) | 2002-06-26 |
| EP1364956B8 (de) | 2006-12-20 |
| ATE334994T1 (de) | 2006-08-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20220627 |